Shelter Island Holidays from AU$837

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Your Shelter Island Holiday

From its highlights to its hidden delights, this city is best explored with a Shelter Island holiday package. Book a hotel in Orient Point, which is great for views, fishing and nature. If your trip to Shelter Island includes some sightseeing, don't miss popular attractions like 67 Steps Beach, Kontokosta Winery and Sag Harbour Marine Park. Check out Expedia's wide range of travel options and start organising your perfect holiday to Shelter Island now.

The Latest Shelter Island Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Iroquois New York

The Iroquois New York

4.5 out of 5
Manhattan
per person
8 Jan - 11 Jan
found 22 hours ago
Return flight included
Seattle (SEA) to New York (JFK)
9.4/10 Exceptional! (1,393 reviews)
My favorite hotel in NYC. Convenient to theater. Lovely rooms. Nice amenities. Very nice staff.

Reviewed on 20 Nov. 2024

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
8 Jan - 11 Jan
found 22 hours ago
Return flight included
Seattle (SEA) to New York (JFK)
9.6/10 Exceptional! (39 reviews)
Boutique hotel atmosphere in the middle of Manhattan

Reviewed on 15 Nov. 2024

The Dominick

The Dominick

5 out of 5
Manhattan
per person
1 Feb - 8 Feb
found 1 day ago
Return flight included
Melbourne (MEL) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
Unfortunately we paid 50 dollars a day for hotel fee but we weren’t allowed to use the sauna

Reviewed on 17 Nov. 2024

CIVILIAN Hotel

CIVILIAN Hotel

4 out of 5
Manhattan
per person
27 Dec - 3 Jan
found 1 day ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (1,624 reviews)
Nice Manhattan hotel. Centrally located.

Reviewed on 21 Nov. 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Our guide on where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.

Find hotel + flight trips in Silver Beach

Shelter Island Holiday

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Wolffer Estates Vineyard, East Hampton Main Beach and 67 Steps Beach

Our pick of the best Shelter Island Hotel Deals

Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 8 Dec to 9 Dec
AU$134
includes taxes & fees
8 Dec - 9 Dec
7.4/10 Good! (1,000 reviews)
"Kind staffs!"

Reviewed on 12 Nov. 2024

Quality Inn Old Saybrook - Westbrook
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 24 Nov to 25 Nov
AU$121
includes taxes & fees
24 Nov - 25 Nov
7.6/10 Good! (891 reviews)
"Everything was satisfactory"

Reviewed on 15 Nov. 2024

Pier Blue Inn Old Saybrook - Essex
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is AU$550 per night from 5 Dec to 6 Dec
AU$550
includes taxes & fees
5 Dec - 6 Dec
8.2/10 Very Good! (604 reviews)
"The staff was very friendly and the receptionist upgraded our room since the hotel was not as busy and it was wonderful."

Reviewed on 5 Nov. 2024

Gurney's Montauk Resort & Seawater Spa
See all 4,669 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Shelter Island holiday package cost?
From just AU$837. Yes, you read that right. Our Shelter Island packages are the easiest way to stretch your budget. Combine your favourite flights, hotels and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Shelter Island?
Book everything all in one place with our Shelter Island holiday packages. We have deals on flights, hotels and more that’ll keep your pocketbook happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1 000 000 properties globally to choose from, you’ll have endless opportunities to mix and match as you want.
What are the top hotels in Shelter Island?
People travelling to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Stunning Waterfront Estate House With 270 Degree Sea Views On 7 Private Acres. You’ll find them in Silver Beach. Another great neighbourhood is Hay Beach. Recently Renovated Mid - Century Modern House In Shelter Island and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are well-liked options in this part of town.
How far in advance should I book my Shelter Island holiday?
While prices do change, we generally recommend booking your flight as soon as possible. Many international airfares are available on Expedia up to 12 months in advance. If you’re booking last minute, you may still get lucky. Cheap journeys to Shelter Island sometimes appear only weeks before departure.
What does an Expedia Shelter Island travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is select your preferred combination. After you’ve made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to customize an awesome Shelter Island holiday.
What should I know before booking a Shelter Island travel package?
Our prices are always low. However, you’ll enjoy even more bargains when you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and loads of choice.
Can I choose my airline with a Shelter Island Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Shelter Island holiday package?
Yes you can, and we’re here to help. You may be able to cancel or amend your Shelter Island holiday package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

What to do in Shelter Island

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

AU$273
Per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.